Substituted oxetanes, method of making, and method of use thereof
a technology of substituted oxetanes and oxetanes, which is applied in the field of substituted oxetanes, can solve problems such as gene expression or function disruption
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example 1
[0159] 2-(Benzotriazol-2-yl)-2-(hydroxymethyl)-3-phenyloxetane (6). Benzotriazole (0.15 g, 1.3 mmol) in dry CH2Cl2 (4 mL) at 0° C. was added to a stirred solution under N2 of 3-phenyl-1,5-dioxaspiro[3.2]hexane (0.21 g, 1.3 mmol) in dry CH2Cl2 (4 mL) at 0° C. The reaction mixture was left to stir for 3 hours at 0° C. It was then concentrated to provide a light brown oil. The residue was purified by flash chromatography on silica gel (petroleum ether / EtOAc 80:20) to give 2-(benzotriazol-2-yl)-2-(hydroxymethyl)-3-phenyloxetane as a white solid (0.15 g, 41%): mp 119-123° C.; IR (film) 3437 (br), 3094, 3064, 2941, 1560, 1499 cm−1; 1H NMR (400 MHz, CDCl3) δ 7.95 (d, J=8.1 Hz, 2H), 7.35 (m, 7H), 5.42 (dd, J=8.7, 7.0 Hz, 1H), 5.20 (dd, J=8.7, 6.0 Hz, 1H), 5.09 (dd, J=6.8, 6.0 Hz, 1H), 4.25 (dd, J=13.0, 7.7 Hz, 1H), 4.20 (dd, J=13.0, 7.0 Hz, 1H), 2.6 (dd, J=7.3, 7.3 Hz, 1H); 13C NMR (100 MHz, CDCl3) δ 144.8, 134.3, 129.3, 128.6, 128.5, 127.8, 119.1, 102.2, 69.8, 63.8, 48.8; MS (EI) m / z 281 (...
example 2
[0160] 2-Hydroxymethyl-3-phenyl-2-(1,2,3-triazol-2-yl)oxetane (7). A solution of 1H-1,2,3-triazole (0.043 g, 0.62 mmol) in dry CH2Cl2 (2 mL) was introduced to a stirred solution under N2 of 3-phenyl-1,5-dioxaspiro[3.2]hexane (0.10 g, 0.62 mmol) in dry CH2Cl2 (2 mL) at −78° C. After 3 hours at −78° C., the reaction was allowed to warm to room temperature; then, the solvent was evaporated in vacuo. The resultant oil was purified by flash chromatography on silica gel (CH2Cl2 / EtOAc 95:5). 2-Hydroxymethyl-3-phenyl-2-(1,2,3-triazol-2-yl)oxetane was isolated as a pale yellow solid (0.076 g, 59%): mp 77.0-78.3° C.; IR (CDCl3) 3145, 3031, 2969, 1496, 1452, 1323, 1049 cm−1; 1H NMR (400 MHz, CDCl3) δ 7.82 (s, 2H), 7.41 (m, 2H), 7.35 (m, 3H), 5.41 (dd, J=8.2, 7.7 Hz, 1H), 5.08 (dd, J=8.5, 6.0 Hz, 1H), 4.98 (dd, J=7.0, 6.0 Hz, 1H), 4.15 (dd, J=13.0, 7.6 Hz, 1H), 4.10 (dd, J=13.0, 7.6 Hz, 1H), 2.51 (t, J=7.6 Hz, 1H); 13C NMR (100 MHz, CDCl3) δ 135.3, 134.1, 128.8, 128.1, 128.0, 99.7, 68.5, 62.9, ...
example 3
[0161] 2-Hydroxymethyl-3-phenyl-2-(tetrazol-2-yl)oxetane (8). 1H-Tetrazole (0.078 g, 1.1 mmol) in dry THF (2 mL) was added dropwise to a stirred solution under N2 of 3-phenyl-1,5-dioxaspiro[3.2]hexane (0.15 g, 0.94 mmol) in dry THF (2 mL) at 0° C. The reaction mixture was stirred for 1 hour and then concentrated. The resultant yellow oil was purified by flash chromatography on silica gel (CH2Cl2 / methanol 100:0 to 98:2) to provide 2-hydroxymethyl-3-phenyl-2-(tetrazol-2-yl)oxetane as a pale yellow oil (0.090 g, 42%): IR (CDCl3) 3436 (br), 2916, 1319, 1054, 953 cm−1; 1H NMR (400 MHz, CDCl3) δ 8.70 (s, 1H), 7.42 (m, 5H), 5.37 (dd, J=8.6, 6.9 Hz, 1H), 5.16 (dd, J=8.6, 6.1 Hz, 1H), 5.08 (dd, J=6.2, 6.2 Hz, 1H), 4.21 (dd, J=13.5, 7.5 Hz, 1H), 4.17 (dd, J=13.5, 7.4 Hz, 1H), 1.86 (dd, J=7.4, 7.4 Hz, 1H); 13C NMR (100 MHz, CDCl3) δ 153.1, 133.2, 129.1, 128.5, 128.1, 100.9, 69.6, 62.6, 47.8; MS (EI) m / z 204 (M+—N2), 185, 173, 104 (100), 91, 78; Anal. calculated for C11H12N4O2: C, 56.89; H, 5.2...
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